Four years after the season four finale, Tree Hill is a new place. Lucas is a struggling writer who is about to embark on a new coaching career with Skills. Peyton is at the beginning of a budding music venture, while Brooke's fashion line is at a crossroads. Meanwhile, Nathan and Haley are young parents trying to find their way. Much has changed in four years, but in many ways, the journey is just beginning.

Lucas' editor wonders about the timing of his recent creative inspiration. Brooke and Peyton make business plans, while Mouth tries to win points with his boss Alice. Lucas and Skills finally make some headway with the Ravens, while Nathan tries to wrestle free from Dan's legacy.